CA1153393A - Elimination du cyanure dans la preparation de produits nitro-aromatiques - Google Patents

Elimination du cyanure dans la preparation de produits nitro-aromatiques

Info

Publication number: CA1153393A
Authority: CA; Canada
Prior art keywords: aqueous; organic phase; compound; acid; mononitroaromatic
Prior art date: 1980-05-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000377430A

Other languages

English (en)

Inventor

Frederick L. Herman

John E. Sawicki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Air Products and Chemicals Inc

Original Assignee

Air Products and Chemicals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-05-19

Filing date

1981-05-12

Publication date

1983-09-06

1981-05-12 Application filed by Air Products and Chemicals Inc filed Critical Air Products and Chemicals Inc

1983-09-06 Application granted granted Critical

1983-09-06 Publication of CA1153393A publication Critical patent/CA1153393A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 24
230000008569 process Effects 0.000 title claims abstract description 18
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title claims abstract description 17
230000009467 reduction Effects 0.000 title description 7
238000006396 nitration reaction Methods 0.000 claims abstract description 24
239000000463 material Substances 0.000 claims abstract description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 21
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 claims abstract description 14
239000012074 organic phase Substances 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
239000008346 aqueous phase Substances 0.000 claims description 9
229910017604 nitric acid Inorganic materials 0.000 claims description 9
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
230000000802 nitrating effect Effects 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
239000006227 byproduct Substances 0.000 claims description 4
230000006872 improvement Effects 0.000 claims description 4
239000012071 phase Substances 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
238000005406 washing Methods 0.000 claims description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
239000000908 ammonium hydroxide Substances 0.000 claims description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
239000001099 ammonium carbonate Substances 0.000 claims 2
239000007864 aqueous solution Substances 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
235000012538 ammonium bicarbonate Nutrition 0.000 claims 1
235000012501 ammonium carbonate Nutrition 0.000 claims 1
235000011114 ammonium hydroxide Nutrition 0.000 claims 1
239000011260 aqueous acid Substances 0.000 claims 1
ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000003513 alkali Substances 0.000 description 7
150000001896 cresols Chemical class 0.000 description 7
GAKLFAZBKQGUBO-UHFFFAOYSA-N 2-methyl-3-nitrophenol Chemical class CC1=C(O)C=CC=C1[N+]([O-])=O GAKLFAZBKQGUBO-UHFFFAOYSA-N 0.000 description 6
239000002699 waste material Substances 0.000 description 6
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 4
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229930003836 cresol Natural products 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000011282 treatment Methods 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
101150071100 CBY2 gene Proteins 0.000 description 1
108010007666 IMP cyclohydrolase Proteins 0.000 description 1
102100020796 Inosine 5'-monophosphate cyclohydrolase Human genes 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000377430A 1980-05-19 1981-05-12 Elimination du cyanure dans la preparation de produits nitro-aromatiques Expired CA1153393A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US151,024		1980-05-19
US06/151,024 US4361712A (en)	1980-05-19	1980-05-19	Cyanide reduction in nitroaromatic process

Publications (1)

Publication Number	Publication Date
CA1153393A true CA1153393A (fr)	1983-09-06

Family

ID=22537019

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000377430A Expired CA1153393A (fr)	1980-05-19	1981-05-12	Elimination du cyanure dans la preparation de produits nitro-aromatiques

Country Status (7)

Country	Link
US (1)	US4361712A (fr)
EP (1)	EP0040429B1 (fr)
JP (1)	JPS5915896B2 (fr)
BR (1)	BR8103073A (fr)
CA (1)	CA1153393A (fr)
DE (1)	DE3163174D1 (fr)
MX (1)	MX159179A (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4482769A (en) *	1983-09-16	1984-11-13	Air Products And Chemicals, Inc.	Reducing 2,4-dinitroortho-cresol in effluent stream from dinitrotoluene process
JPS6134162A (ja) *	1984-07-26	1986-02-18	Kobe Steel Ltd	金型用プレハードン鋼の製造方法
US4597875A (en) *	1985-05-07	1986-07-01	Air Products And Chemicals, Inc.	Precipitative removal of nitrocresols from dinitrotoluene waste streams
US4604214A (en) *	1985-08-16	1986-08-05	Air Products And Chemicals, Inc.	Removal of nitrocresols from dinitrotoluene waste streams using fentons reagent
US5221440A (en) *	1992-04-20	1993-06-22	Rubicon Inc.	Process for destruction of nitro-hydroxy-aromatic compounds in aqueous media
FR2714666B1 (fr) *	1993-12-31	1996-03-01	Rhone Poulenc Chimie	Procédé d'élimination d'effluents aqueux comprenant notamment des composés hydroxynitroaromatiques.
US5762802A (en) *	1997-05-01	1998-06-09	Air Products And Chemicals, Inc.	Dilute acid oxidation of dinitrotoluene alkaline wash water
DE10345601A1 (de) *	2003-09-29	2005-05-12	Basf Ag	Verfahren zur Entfernung von Nitrokresolen aus Abwasser der Mononitrotoluolherstellung und zur weiteren Verwendung des Extraktes
PL2841412T3 (pl)	2012-04-25	2016-10-31		Sposób przemywania dinitrotoluenu
US9249083B2 (en)	2012-04-25	2016-02-02	Basf Se	Process for scrubbing dinitrotoluene
WO2015032706A1 (fr) *	2013-09-05	2015-03-12	Basf Se	Procédé d'élimination de hcn à partir de dinitrotoluène brut
HUE040622T2 (hu)	2013-10-22	2019-03-28	Basf Se	Eljárás dinitrotoluol savas mosására hidrogéncianid jelenlétében

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL32365C (fr) *	1931-07-27
US2132845A (en) *	1936-09-12	1938-10-11	Du Pont	Process for purification of trinitrotoluene
US2382133A (en) *	1943-03-27	1945-08-14	Du Pont	Manufacture of trinitrotoluene
GB939873A (en) *	1961-09-19	1963-10-16	Ici Ltd	Manufacture of dinitrotoluene
NL124301C (fr) *	1962-02-09	1968-05-15
US3185738A (en) *	1962-11-01	1965-05-25	Du Pont	Preparation of meta-dinitrobenzene by a two-stage nitration process
DE1468362A1 (de) *	1964-10-23	1968-11-28	Meissner Fa Josef	Zweistufige Anlage zur Nitrierung von aromatischen Kohlenwasserstoffen
US3981933A (en) *	1974-07-08	1976-09-21	General Electric Company	Process for making dinitrotoluene
US3957889A (en) *	1975-05-02	1976-05-18	Air Products And Chemicals, Inc.	Selective nitration of aromatic and substituted aromatic compositions
DE2704680A1 (de) *	1977-02-04	1978-08-10	Bayer Ag	Verfahren zur gewinnung von aromatischen dinitroverbindungen

1980
- 1980-05-19 US US06/151,024 patent/US4361712A/en not_active Expired - Lifetime
1981
- 1981-05-12 CA CA000377430A patent/CA1153393A/fr not_active Expired
- 1981-05-18 BR BR8103073A patent/BR8103073A/pt unknown
- 1981-05-19 JP JP56075591A patent/JPS5915896B2/ja not_active Expired
- 1981-05-19 MX MX187396A patent/MX159179A/es unknown
- 1981-05-19 DE DE8181103842T patent/DE3163174D1/de not_active Expired
- 1981-05-19 EP EP81103842A patent/EP0040429B1/fr not_active Expired

Also Published As

Publication number	Publication date
JPS5711945A (en)	1982-01-21
DE3163174D1 (en)	1984-05-24
MX159179A (es)	1989-04-28
US4361712A (en)	1982-11-30
EP0040429B1 (fr)	1984-04-18
EP0040429A1 (fr)	1981-11-25
JPS5915896B2 (ja)	1984-04-12
BR8103073A (pt)	1982-02-09

Legal Events

Date	Code	Title	Description
2000-09-06	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20000906

Publication	Publication Date	Title
KR101093862B1 (ko)	2011-12-13	디니트로톨루엔의 제조 과정에서 수득된 폐수의 처리 방법
CA1153393A (fr)	1983-09-06	Elimination du cyanure dans la preparation de produits nitro-aromatiques
US5756867A (en)	1998-05-26	Recovery of nitric acid from nitration processes
US7470826B2 (en)	2008-12-30	Recovery of nitrating acid mixtures from nitration processes
US9540313B2 (en)	2017-01-10	Method and apparatus for purifying nitration products
KR101917384B1 (ko)	2018-11-09	디니트로톨루엔으로부터 불순물을 제거하는 방법
KR101093972B1 (ko)	2011-12-15	디니트로톨루엔의 제조에 있어서 2차 성분의 처리 방법
US4482769A (en)	1984-11-13	Reducing 2,4-dinitroortho-cresol in effluent stream from dinitrotoluene process
US4496782A (en)	1985-01-29	Nitric acid recovery by the adiabatic nitration of nitroaromatics with fortified spent acid
KR100271538B1 (ko)	2000-11-15	약산을 이용한 디니트로톨루엔의 제조 방법
US4918250A (en)	1990-04-17	Process for the production of dinitrotoluene using an inorganic salt as a phase separation agent
US9249083B2 (en)	2016-02-02	Process for scrubbing dinitrotoluene
US5395995A (en)	1995-03-07	Process for the preparation and purification of nitroaromatics
CA2871543A1 (fr)	2013-10-31	Procede de lavage de dinitrotoluene
US4650912A (en)	1987-03-17	Recovery of nitric acid from nitration spent acid by toluene extraction
US6254789B1 (en)	2001-07-03	Method for treating aqueous solutions comprising acids and nitrated compounds
US4642396A (en)	1987-02-10	Process for separating nitroaromatic compounds from spent nitric acid
US5820764A (en)	1998-10-13	Treatment/removal of byproduct aqueous effluents comprising hydroxynitro-aromatic compounds
US5354924A (en)	1994-10-11	Process for the production of dinitrotoluene
US6191325B1 (en)	2001-02-20	Recovering/recycling nitric acid from dinitration process streams comprising HNO3/dinitro compounds
US5874654A (en)	1999-02-23	Purification of mixtures of nitroaromatic compounds by removing nitrocresols therefrom
EP0047331A1 (fr)	1982-03-17	Récupération des composés aromatiques nitro à partir des lessives de nitration
EP0649400A1 (fr)	1995-04-26	Procede de production de dinitrotoluene
JPS6249259B2 (fr)	1987-10-19